704890-52-8Relevant academic research and scientific papers
Determination of enantiomeric purity of hydroxy biaryls using1H and31P-NMR on their diazaphospholidine derivatives
Alexakis,Frutos,Mangeney,Meyers,Moorlag, Henk
, p. 5125 - 5128 (1994)
Chiral biaryl alcohols were readily transformed in a single step, with chiral non-racemic 1,2-diamines, PCl3, and sulfur in CDCl3 - all in a NMR tube - to their diastereomeric diazaphospholidines and their diastereomeric ratios (also
Synthesis, resolution, and application of 2,2′-bis(diphenylphosphino) -3,3′-binaphtho[b]furan (BINAPFu)
Andersen, Nell G.,Parvez, Masood,McDonald, Robert,Keay, Brian A.
, p. 145 - 161 (2007/10/03)
(±)-2,2′-Bis(diphenylphosphino)-3,3′-binaphtho[2,1-b] furan (BINAPFu) was synthesized from 2-naphthoxyacetic acid in a five-step sequence in 62% overall yield. A variety of reported resolution procedures for biaryl bisphosphines did not work with (±)-BINAPFu; thus, a new resolution method was developed, involving the Staudinger reaction of the aforementioned racemate of BINAPFu with an enantiopure camphor sulfonyl azide derivative. The resulting diastereomeric phosphinimines were separated by flash chromatography. Subsequent hydrolysis to the corresponding bis-phosphine oxide and trichlorosilane reduction provided enantiopure BINAPFu. The absolute stereochemical configuration of BINAPFu was established by X-ray crystallography. BINAPFu was compared with commercially available 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP) in Pd(0)-catalyzed intermolecular Heck reactions. Investigation of the Heck arylation of 2,3-dihydrofuran showed BINAPFu to be more efficacious than BINAP in dioxane at 30°C. A variety of phosphorus selenides were prepared, and the 1JP-Se coupling constants measured, to obtain a comparative scale of parent phosphine basicity. The phosphorus atoms in BINAPFu were found to be electron deficient when compared with BINAP but slightly more electron rich than trifurylphosphine.
